


The Best-Laid Pranks

by Winter_of_our_Discontent



Category: Supernatural
Genre: Alternate Universe - Normal Life, Lawyer Sam Winchester, Multi, Prank Wars
Language: English
Status: Completed
Published: 2016-01-14
Updated: 2016-01-14
Packaged: 2018-05-13 23:32:12
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,785
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5721160
Author URL: https://archiveofourown.org/users/Winter_of_our_Discontent/pseuds/Winter_of_our_Discontent
Summary: <blockquote class="userstuff">
              <p>Sam Winchester knows that prank wars with his brother Dean are stupid and immature.</p>
<p>He also knows he's playing to WIN.</p>
<p>...But he may not have thought this one through.</p>
            </blockquote>





	The Best-Laid Pranks

The last straw was Dean packing his showerhead with some sort of sparkly bath bomb. Two weeks later and he was still finding glitter in his hair. (Though he did kind of enjoy the lavender scent.)

 

They were both-- Sam knew this, he’d had various girlfriends mention it from time to time-- way too old for prank wars, but it was a tradition, and Winchesters were all about traditions. Stupid traditions, mostly, but traditions all the same.

 

He couldn’t even remember what started this round, just that there was no backing down now. The problem was that after twenty-ish years, it was hard to think up things that hadn’t been done already, or that Dean wouldn’t see coming a mile away.

 

And he should be thinking about the briefs he needed to file later, but instead, here he was, thirty, a fancy-pants lawyer (as Dean still called it) on his way to his office, trying to figure out how many Post-it notes it would take to cover the entire surface of a 1967 Chevy Impala.

 

He angled his bike into the first empty elevator he saw, but before he hit the floor button he heard someone calling out his name and moved to press the open door button instead. 

 

“Thanks, Winchester,” Meg Masters said, dressed as usual in black and red with stiletto heels. She punched the thirteenth floor (Corporate law) with enough force that Sam winced.

 

“Thank you, Sam,” Castiel Novak stepped in behind her, carefully holding a tinfoil-covered pan of what looked like baked goods.

 

“What is it today, Clarence?” Masters asked, eyeing the pan and then the forensic accountant as though she’d be interested in devouring either of them.

 

Novak was a good guy, but he was awkward. If you put numbers in front of him he was fine-- probably what made him such a great forensic accountant-- but he was much less skilled with other people. So Masters’ flirting seemed to go right over his head. “It’s Becky’s birthday. I made her cupcakes.” 

 

“Ooo, buttering up the receptionist, eh? You sweet on her?” 

 

“She is a valuable member of the firm and I would like her to know that her hard work is appreciated,” Novak replied, straight-faced. “But if you’re asking if I’m trying to express a romantic interest in her, you should know that she is currently dating the night watchman Chuck.”

 

“So… any women here you do have your eye on, angel? ‘Cause I should let you know I’m single and  _ very _ partial to red velvet.”

 

Sam couldn’t tell if Castiel was uncomfortable yet, but  _ he  _ was definitely wishing he worked on a lower floor. Or had taken the stairs.

 

“Given that I am exclusively attracted to men, having my eye on any of the women working here would be counterproductive to both of us.”

 

Huh. Sam had not known that. It was fine of course, he just… hadn’t known that.

 

“Dammit, all the good ones  _ are _ taken or gay,” Master said, pouting. “Well, you remember red velvet for my birthday just the same.”

 

Sam would never have admitted it, but he spent the rest of the now blessedly silent ride eying Castiel trying to decide if he was attractive and wondering if Castiel found him attractive. 

 

Castiel seemed alright, for a guy, if you were into guys, which Sam wasn’t. He was smart, good job, attractive enough, as far as Sam could tell, and he baked really well, which was probably a plus for anyone. Hell, even Dean, who was straighter than the lines on a legal pad, would probably have...

 

Wait.

 

Shit. No.

 

And yet.

 

But.

 

On the other hand.

 

It was a horrible idea.

 

He was a horrible person for even thinking about it.

 

But.

 

It was the  _ perfect prank _ .

 

First he would need to put Dean off his guard. He needed another prank… small enough that Dean won’t feel the need to immediately retaliate but big enough that Dean would assume that Sam was done for a while. Then Sam would strike.

 

Sam felt bad about it, almost. Because Castiel was a good guy. But he was counting on two things: one was that Castiel was socially clueless enough that he probably wouldn’t even register the date going wrong. And two was that Dean, for all his asshole big brother tendencies, wasn’t going to be a complete jerk to a guy he didn’t know, especially when he realised that Sam was the mastermind behind the prank.

 

He waited until Masters had stepped out of the elevator.

 

“Hey, uh, Castiel, could I talk to you for a minute?”

 

***

 

He’d managed Step One, which was getting Castiel to agree to a blind date with his brother. 

 

Timing would be everything for Step Three, the most delicate part of the operation, mostly due to the success of Step Two, which had involved covering the floor of Dean’s bedroom in a layer of shaving foam filled balloons while he slept.

 

Sam waited until a week had passed, until an evening when they were both mellow in the aftermath of lasagna, a couple of bottles of beer, and were sprawled out on the couch halfway through  _ Jaws _ . “So, uh, Dean?”

 

“Yeah?”

 

“There’s someone at work.”

 

“Oh ho, you finally meet someone?” Dean pretended to wipe a tear from his eye. “They grow up so fast…”

 

Sam rolled his eyes, but kept to his script. “No, uh, actually… I thought you might be interested. I mean, it’s been awhile since you’ve gone on any dates.”

 

“Says the monk,” Dean grumped. “Been too busy with classes and you know it. ‘sides, I know better than to date a lawyer.”

 

“Castiel is one of our forensic accountants. Best at the firm. Incredibly smart.”

 

“Hot?” Dean finally asked.

 

“Very,” Sam said.  

 

“So why’s she need a hook up?” Dean said, a note of suspicion entering his voice. “What’s wrong with her?”

 

“Castiel is just… kinda shy. A little awkward around people.”

 

“So why aren’t  _ you _ interested?”

 

Sam shrugged. “More your type than mine. Dark hair, bright blue eyes, likes to bake… brought in a pie for someone’s birthday last week.” 

 

Dean’s eyes lit up at the last part, though he did his best to keep his voice grumpy. “I dunno, Sam…”

 

“Please?” Sam said, turning the full force of his most pleading expression on Dean. Dean didn’t stand a chance, and they both knew it as he cracked under the weight of Sam’s gaze. “I just… it’d be good for you to get out. I worry about you.”

 

Dean looked away. Victory! “Fine, fine, you don’t have to write the best man speech, I’m in.”

 

“Great!” Sam said, slapping Dean on the shoulder. “I’ll set up everything.”

 

***

 

“You have the directions?”

 

“Yeah, yeah, I’m all set for your stupid gastropub,” Dean said as he stepped out from his room. “Dude, you’re more into this date than I am.”

 

“I just want things to go perfect,” Sam said, and then stopped as he saw Dean’s outfit. 

 

He’d gone all out, by Dean standards, with a charcoal grey blazer over a deep green button down and the jeans he always claimed must’ve shrunk in the wash. Freshly shaved, hair styled in a way that Sam knew from sharing a bathroom with him took about half an hour, and Sam even caught a whiff of aftershave as Dean breezed by, grabbing his keys and leather coat. “It’ll be fine. Later, Sammy.”

 

Sam opened his mouth to say something, because he was starting to wonder if just maybe he’d gone too far. 

 

But then the door slammed, and Dean was gone, followed moments later by the unmistakeable sound of the Impala’s engine driving off into the night.

 

Towards the date.

 

Shit, what had he done? Dean was actually  _ trying _ . Dean had been single for over a year now, and Dean genuinely wanted this date to go well, and Dean had trusted  _ him _ to have found someone he thought Dean would like, and it was going to go horribly and Dean would remain sad and alone and single for the rest of his life all because of a stupid  _ prank _ .

 

Sam collapsed onto the couch.

 

What could he do now, though? Dean was on his way, Castiel was probably already there, and Sam commuted or biked everywhere. 

 

Shit, and he’d gotten Castiel involved too. He was a nice guy, a good worker, whose only problem had been getting inadvertently stuck in the middle of some stupid, juvenile prank war between Sam and his brother. 

 

Sam offered up a silent prayer that Dean wouldn’t say or do something dickish to Castiel because he was pissed at Sam.

 

He sighed, letting his head flop backwards against the couch. 

 

From his vantage point, he could see the the microwave, its numbers glowing at him reproachfully. He watched with the air of a condemned man as the minutes slowly advanced. Dean must’ve be there by now. What was going on? Had he met Castiel yet? Realised he’d been set up by Sam? Was he yelling? Had he stormed out of the restaurant? Was he heading back here?

 

Sam grew tenser and tenser as ten minutes passed, then thirty. 

 

He filled a glass with tap water.

 

He should do something.

 

He couldn’t think of anything to do.

 

He remembered that he’d left the glass of water next to the sink. He retrieved it.

 

He could get Dean a bottle of his favorite whiskey, the expensive stuff he’d never buy for himself.

 

Sam turned the TV on. Dean had left it turned to Food Network. Sam couldn’t bring himself to change the channel from Cupcake Wars, as though leaving it there was some bizarre form of penance.

 

An hour.

 

He remembered to drink the now room temperature water. It tasted flat and metallic.

 

An hour and fifteen. On the TV, someone did something impressive with sugar.

 

He’d need to apologise to Castiel too. How did you apologize for something like this? He couldn’t just send him a fruit basket.

 

He thought he’d heard Castiel mention liking guinea pigs once, and had a sudden vision of sending a bouquet of those to their workplace. The thought set off a stream of nervous giggles.

 

Could you get written up by HR for pranking a co-worker?

 

Oh god he was going to get fired.

 

An hour and a half, now. What had happened? Where the hell was Dean?

 

He jumped several inches off the couch when his phone suddenly beeped.

 

Slowly, gingerly, his eyes squeezed shut, he picked it up off the cushion next to him. He forced one eye open. 

 

One new text. From Dean. 

  
_ Thanks Sammy didn’t know you knew. Cas is incredible. Don’t wait up! _

**Author's Note:**

> Based on this Tumblr prompt: http://freecas.tumblr.com/post/125763545499/ok-so-imagine-sam-trying-to-prank-dean-by-setting
> 
> As always, my love to vulgarweed, pg, and RA for their help and support, and to lareinenoire for the title.


End file.
